The only Roguelike I ever enjoyed playing was Liberal Crime Squad. The gameplay can be extremely frustrating (it is a roguelike), but there are so many crazy things which are possible that it remains a fountain of amusement. Some examples from TVTropes:

While not everything is covered some highly unlikely law combinations are acknowledged. The game tracks base sex as well as chosen ones. If at Elite Liberal Gay Rights but at Conservative or lower Women's Rights the bouncers will allow a base female designated male in the Gentlemen's club without a disguise check. Implying that while women are second class citizens, LGBT rights are so ingrained that they accept transmen without any effort put into passing.

If the game goes on long enough, everything remains the same mechanically, but things get renamed - Nightsticks become Electro-Shock Sticks, Spraypaint becomes Holo-Paint, Pitchforks become Space Pitchforks, Gavels become Laser Gavels, etc.

The more you succeed in making gun control a reality, the harder it is to get weapons for your raids. Pawn shops will stop carrying certain weapons and jack up their prices on those that remain. Gang members will still sell you guns, but their prices go up exponentially as well.

Making police laws elite liberal will cause them to be accompanied by moderate Police Negotiators, which makes the game much harder (because now, if you fight them, you'll risk alienating public opinion by injuring a moderate.)

While most obsoleted professions from more conservative law levels disappear some may hang around, resulting in the occasional death squad member at the police station